Desktop Systems Administrator II

Join us in bringing joy to customer experience. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide.

Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves.

The Desktop Systems Administrator II serves as an advanced Tier II escalation point, responsible for deploying, maintaining, and supporting enterprise endpoint hardware, operating systems, and core productivity applications. This role partners closely with Service Desk and Infrastructure teams to ensure high availability, streamline standard operating procedures, and deliver white-glove technical support to on-site, remote, and executive personnel. This position requires being in the office 5 days per week at our Dallas, TX location.

Key Responsibilities

Technical Support & VIP Services

• Tier II Incident Resolution: Act as an escalation point for complex incidents and service requests from the Service Desk, troubleshooting hardware, software, VPN, mobile devices, peripherals, and network connectivity across Windows and macOS environments.
• Executive & VIP Support: Deliver high-touch, urgent technical support for senior leadership and administrative staff with minimal business disruption.
• Incident & Outage Management: Monitor, prioritize, and resolve ticketing queues within established SLAs; participate in an on-call rotation to resolve critical after-hours incidents and outages.
• Event & AV Support: Configure, test, and facilitate audio/video conferencing solutions (e.g., Zoom Rooms, Microsoft Teams, etc.) for executive presentations and company-wide meetings.
• Working with IT Engineering teams, act as “smart hands and eyes” for in-office infrastructure including networking equipment and servers

Endpoint & Systems Administration

• Endpoint Provisioning & Deployment: Deploy, configure, and maintain laptops, desktops, and mobile devices using enterprise management tooling (e.g., Intune, Jamf, SCCM).
• Identity & Access Management: Administer user accounts, groups, and device policies within Microsoft Entra ID (Azure AD) and Okta.
• Task Automation: Familiarity with technologies to automate repetitive administrative workflows and system maintenance tasks through scripting or AI.
• Infrastructure Relocations: Coordinate and execute IT workspace setups, office reconfigurations, and moves/adds/changes.

IT Asset Lifecycle Management (ITAM)

• Hardware Lifecycle Operations: Maintain the end-to-end hardware lifecycle, including procurement staging, bench testing, provisioning, secure data sanitization/wiping, and e-waste disposal.
• Inventory Control: Monitor and maintain stock levels for hardware, peripherals, and accessories across local depots in alignment with organizational standards.

Process Improvement & Knowledge Management

• SOP Development: Document standardize operating procedures, knowledge base articles, and end-user self-service guides to increase First Contact Resolution (FCR) rates.
• Cross-Functional Collaboration: Partner with Infrastructure, Security, and Desktop Engineering teams to identify operational gaps, rollout technology updates, and enforce IT standards.

Qualifications & Requirements

Required Experience & Education

• Education & Experience: Bachelor’s degree in Information Technology, Computer Science, or equivalent practical experience with 5+ years of progressive end-user computing / desktop support experience.
• Executive Support: Minimum 2 years of experience providing dedicated VIP / executive-level technical support.
• Operating Systems & Software: Deep administration knowledge of Windows and macOS, along with enterprise suites (Microsoft 365, Google Workspace, Adobe Creative Cloud, Slack, Zoom).
• Endpoint Management: Comprehensive knowledge administering devices via MDM/UEM platforms (e.g., Microsoft Intune / Endpoint Manager, Jamf Pro, or SCCM).
• Identity & Directory Services: Practical experience managing users, access permissions, and device compliance in Microsoft Entra ID (Azure AD) and Okta.
• Networking Fundamentals: Strong comprehension of enterprise network protocols and services (TCP/IP, DNS, DHCP, VPN, Wi-Fi 802.1x).
• Communication & Professionalism: Outstanding written and verbal communication skills; proven ability to translate complex technical concepts into clear, accessible language for non-technical stakeholders.
• Physical Requirement: Ability to physically lift, rack, move, and deploy hardware weighing up to 50 lbs.

Preferred Additional Qualifications

• Certifications: CompTIA A+, Network+, Security+, Microsoft 365 Certified: Endpoint Administrator Associate, or Jamf Certified Associate.
• Scripting Skills: Working knowledge of PowerShell, Bash, or Python for desktop administration and deployment automation.
• AI fundamentals of Claude, ChatGPT, Gemini or other AI platforms.
• ITIL Familiarity: Understanding of ITIL framework and ticketing workflows (e.g., ServiceNow, Jira Service Management).

Work Location: This role is hybrid. 3 days a week (T, W, TH) in our Dallas office is required.

As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process. Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.

Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Our total reward package also includes:

• Health, dental, and vision coverage, beginning on the first day of employment. Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost. We also offer Short & Long-Term Disability, Basic Life Insurance, and a 401k saving plan with employer matching.
• Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
• Generous employee stock purchase plan.
• Paid Time Off, Company paid holidays, paid volunteer hours and 12 weeks paid parental leave.

All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.

The US base salary range for this role is below.

$72,100—$200,200 USD

Five9 embraces diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better we are. Five9 is an equal opportunity employer.

Five9 is committed to providing reasonable accommodations for qualified individuals with disabilities throughout the application and interview process. If you need assistance or an accommodation due to a disability, please contact us at View email address on aiapply.co to request an accommodation. Requests will be handled confidentially and in accordance with applicable law.

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Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.